3-ethoxycarbonyl-3-ethoxycarbonylmethyl-5-fluoro-2-tosylisoindolin-1-one | 1356832-71-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethoxycarbonyl-3-ethoxycarbonylmethyl-5-fluoro-2-tosylisoindolin-1-one
• 英文别名: Ethyl 1-(2-ethoxy-2-oxoethyl)-6-fluoro-2-(4-methylphenyl)sulfonyl-3-oxoisoindole-1-carboxylate
• CAS: 1356832-71-7
• 化学式: C₂₂H₂₂FNO₇S
• 分子量: 463.484
• InChiKey: NHPCWSLVFQSLSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  重氮乙酸乙酯 、 4-fluoro-N-tosylbenzamide 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以82%的产率得到3-ethoxycarbonyl-3-ethoxycarbonylmethyl-5-fluoro-2-tosylisoindolin-1-one
  参考文献：
  名称：

  Rhodium catalyzed synthesis of isoindolinones via C–H activation of N-benzoylsulfonamides

  摘要：

  An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [{RhCl2Cp*}2] enables the in situ dimerization of diazoacetate in addition to its role in catalyzing C-H functionalization/cross-coupling. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.095

文献信息

• Rhodium catalyzed C–H olefination of N-benzoylsulfonamides with internal alkenes
  作者：Chen Zhu、John R. Falck

  DOI：10.1039/c2cc16963k

  日期：——

  An annulation via tandem rhodium catalyzed C–H olefination of N-benzoylsulfonamides with internal olefins followed by C–N bond formation is disclosed. A N-substituted quaternary center is formed during the reaction thus providing efficient access to a series of 3,3-disubstituted isoindolinones.

  通过双重铑催化的C–H烯化反应，将N-苯酰磺酰胺与内部烯烃进行环化，接着形成C–N键。这一反应过程中形成了N-取代的四价中心，从而高效地合成了一系列3,3-二取代的异吲哚啉酮。
• Rhodium catalyzed synthesis of isoindolinones via C–H activation of N-benzoylsulfonamides
  作者：Chen Zhu、John R. Falck

  DOI：10.1016/j.tet.2012.08.095

  日期：2012.11

  An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [RhCl2Cp*}2] enables the in situ dimerization of diazoacetate in addition to its role in catalyzing C-H functionalization/cross-coupling. (C) 2012 Elsevier Ltd. All rights reserved.